How a Shoemaker Turned Into a Spy

One of America’s first spies, a cobbler from Putnam County named Enoch Crosby, remains largely unknown

By David Levine

Courtesy of Jay Heritage Center

Sun Tzu, the sixth century B.C. military genius behind The Art of War, knew the value of a good spy. “What enables the wise sovereign and the good general to strike and conquer, and achieve things beyond the reach of ordinary men, is foreknowledge,” he wrote. “Now this foreknowledge cannot be elicited from spirits; it cannot be obtained inductively from experience, nor any deductive calculation. Knowledge of the enemy’s dispositions can only be obtained from other men. Hence the use of spies...”

As long as hominids have been fighting one another, they have been snooping on one another. Espionage has been called the world’s second-oldest profession. Famous spies, both real and fictional, have been lauded by their sponsors and vilified by their enemies from the Trojan Horsemen up to James Bond and George Smiley. During the Revolutionary War, Benedict Arnold became the very model of the turncoat, and his name has lived in infamy here for more than two centuries.

But Arnold had a counterpart, a man from the Hudson Valley who was one of the first American spies. And you most likely have never heard of him.

A man of “special abilities”

His name is Enoch Crosby. He was born in Massachusetts on January 4, 1750, and moved to what is now Putnam County when he was still very young. At the age of 16 he became an apprentice shoemaker in Kent, and was plying his trade in Danbury, Connecticut, when the Revolutionary War broke out. He enlisted with a Connecticut regiment and took part the invasion of Canada in 1775. He then returned to Danbury to make shoes, but the call of war drew him back to the army in 1776. He was on his way to an encampment in White Plains when he found his true military calling.

Westchester County was, at that time, a kind of no-man’s land, with the British Army in New York City and the colonial militias to the north. Supporters of both sides roamed Westchester. Crosby was mistaken as a Loyalist and asked to meet with others to join the Tory cause. He took what he learned to John Jay, who was a member of the local Committee of Safety, and together they had the Loyalists arrested.

Jay asked him to become a full-fledged spy, reportedly telling him that “our greatest danger lies in our secret enemies. A man of your special abilities is entitled to greater credit than a regular soldier.” This recruitment made Crosby one of the country’s first intelligence agents — predating the CIA by more than 150 years.
Crosby in fact became a double agent, pretending to be a British spy in order to infiltrate the Loyalists. No one, not even his family, knew he was working for the colonial cause; Crosby asked the Committee of Safety to promise that, if he was killed, his name would be cleared. He also received a special pass to be used if he was captured by American forces.

Crosby was quite successful. He roamed the Hudson Valley and upstate New York from Westchester County to Lake Champlain, infiltrating Loyalist groups and returning with valuable information. He was also captured by Americans at least four times. One of those times, “he was traveling to Kings Bridge, with men who said they were going to enlist with the British Army,” says Willa Skinner, who is the historian for both the Town of Fishkill and the First Reformed Church of Fishkill. “He led them to the church, where they were all arrested — including Crosby.” A few miles away, he stood a mock trial at the Van Wyck Homestead, then he was released and sent on another mission.

All the while, Crosby maintained his cover as an itinerant cobbler and peddler. He spent the better part of six years moving between American and British sympathizers, living in deprivation — he sometimes had to hide and sleep in caves — and suffering beatings and even condemnations of death. He had to slink about at night, and had very few people with whom he could confide or find safety.

One of the only places Crosby found respite was at the home of Colonel Henry Ludington, the commander of the Seventh Dutchess County Militia. Col. Ludington’s daughters — including the famous Sybil — may have helped their father communicate with Crosby and other spies, serving as both guards and liaisons between them.

“Spy” vs. spy

After the war, Enoch and his brother, Benjamin, bought 276 acres of farmland near Brewster from the Commission of Forfeiture. Enoch married Sarah Kniffen in 1785; after she died in 1811, he married Margaret Green, who died in 1825. Crosby himself died on June 26, 1835, and was buried next to his first wife in the Old Gilead Cemetery in Carmel. Near the end of his life, he wrote in a letter, “Having been spared to enjoy these blessings — independence and prosperity — for half a century and see them still continued, I can lay down my weary and worn out limbs in peace and happiness.”

He also enjoyed a small amount of fame. After the war, John Jay, who became the first chief justice of the Supreme Court, had an equally famous neighbor: writer James Fenimore Cooper. In 1821, Cooper published The Spy, a book that chronicles the exploits of a fictional character named Harvey Birch who is remarkably like Crosby. “Cooper never confirmed that Harvey Birch was really Enoch Crosby,” says Skinner, “but since John Jay told Cooper many stories of the Revolution, we have to assume.”

The book earned Crosby a bit of notoriety. He is further honored now with a portrait in the National Gallery in Washington, D.C. Locally, he is remembered inside the Van Wyck Homestead, which is considered the setting for The Spy. There is also a marker outside the First Reformed Church in Fishkill, where he was confined for the trial; and another on the west side of Route 6 in Southeast, between Drewville Road and Route 312, that reads, “Enoch Crosby, patriot spy of the American Revolution, lived on a farm, given him for his service, on the west side of this reservoir.” And “there are a lot of Crosbys still around the region,” says Skinner, along with an Enoch Crosby Chapter of the DAR in Putnam County.

What made him such a good spy? “It must have been his personality,” Skinner says. “He pretended he was a humble shoemaker, and it allowed him to get in with all the locals, whether they were patriots or not.” It’s unknown how many Loyalists Crosby helped capture; “my answer would be, a lot,” says Skinner. And though he never earned the fame that the Founding Fathers and other better-known patriots enjoyed, his service as a covert operative was greatly appreciated. “George Washington would say he was a hero,” says Skinner.